Dating Disaster #1 or, the importance of red flags

So I was having dinner with my friend Mike today and telling him about the bad date I went on the other day. He suggested I write about it in my blog. We then had a whole discussion about the need for self-disclosure, private made public, internet voyeurism etc. which is a whole other blog I have been thinking about writing.
But, I had been thinking about writing a separate, more anonymous blog about my dating history anyway so that I could write about some of my more intense dating debauchery...but, I have insomnia now and I need to blog more (does anyone actually need to blog at all?). So here it is.
So R., as are most of my dates, was a splendid craigslist find from an ad I posted on the 4th of July. As I was leaving another date that had been a pretty solid failure I checked my email from my phone. I had gotten an email from this guy, he seemed nice and his pic was cute, kind of dorky, I thought maybe he could have some potential. And after my dating disgrace I was ready for another date. Turns out he was up near Harlem, and at the time I was in the East Village so I suggested we meet in Union Square. I figured I would walk there, wait for a bit and then he would show up. Well, after nearly an hour and a half of waiting he didn't show and I left. He texted as I was getting home and apologized for taking so long to get down there and said he would still like a chance to meet me. We emailed a little bit and I wasn't really feeling it, especially after he did what I hate which is the "check-in" email: "Hey, didn't hear back from you..just wondering...you know...if you got my last email." It gets to be a little much for me.

However, after all of these red flags of qualities that i know I don't like, I still decided to go through with a date. So Monday we were supposed to meet at a restaurant near my house at 6. I got a voicemail from him at 5:30 telling me to call him back (no other relevant info, which I also hate), I called back, got no answer and headed to the restaurant a little after 6. As I'm walking there he calls me telling me he had JUST gotten out of work (in Harlem) and was just leaving. Why he did not share this information in his first message I do not know. I was pretty much over it by this time, but he was already on his way and I could deal with some free dinner (that's right, not going dutch on this one).
So he calls me when he gets off of the subway and tells me he doesn't remember the name of the restaurant or where it is, I tell him to just go up one block to Leonard. He gets kind of whiny, saying he has no sense of direction.
Ok, I also have no sense of direction, but as with any disability you learn to adapt. In this particular situation I would go one block, if that wasn't the street, I would turn around and go the other way one block. One of those would be the street, see? But, our man R obviously is an idiot with no problem solving skills. So I go rescue him from the corner and we go to the restaurant.
I was already pretty unimpressed, so I don't know if there is a lot he could have done to redeem himself. But he didn't help himself at all. He didn't really look like his picture. He was recognizable, but was a lot nerdier in person.
First of all, his conversational skills were severely limited and he changed topics really bizarrely in a way that was really hard to follow. You also have to imagine a really monotone/shy voice with limited affect. An example of a conversational tidbit:
Him: What tv shows do you like.
Me: Um, I've been watching this show that ran on SciFi like a year ago called The Dresden Files.
(note: this is an example of why I am excellent at dating [not choosing dates obviously. but the actual act itself, I rule]. I chose this show in particular because I figured he would probably be into scifi)
Him: Like the city in Germany?
Me: Um, yeah, but it's the guy's last name.
Him: I just read a book about Dresden.
Me: ...

So, just a lot of that, where it's not completely off topic, but it's not how normal people would progress a conversation.

Anyway, I can deal with awkward, I'll just suck it up and get through my date and whatever. But then it gets worse.
We are talking about scary movies and I mention that someone I knew was so scared by The Ring that she had to sleep in her mom's bed for a week (at age 20+)
His response? "Oh, you could sleep in my bed if you needed to"
ugh.
I'm not a big fan of sexual innuendo in casual conversation with people I don't really know in the first place. Add in all of this dude's qualities and I spent the whole meal cringing.


So after dinner we decide to go get gelato at this window service place. We are standing in line and R asks if there is anywhere to sit and I tell him that there are chairs around the corner.
Him: Oh, haha, I was going to say something kind of suggestive. But maybe I won't...
Me: Ok.
Him: Do you want to hear it?
Me: Do you want to get shot down? (Yes I did say this)
Him: I was going to say something about...you know....going back to your place...and you know...eating gelato.
Me: We can just eat here.

Then as we're getting ready to order he announces that he's going to get a pint. I was like, jesus, but ok. Then he asks what size I am getting, I tell him a small. He says he will get a small too, but still orders the pint.
He gets his huge pint of gelato, which, as luck would have it was scooped in such a way that it had two ice cream scoop round mounds on the top.
Him: "Oh haha, look...this looks like something"
Me: ...
As we are eating he asks me if his size is a small. No, I say, it is a pint. You ordered a pint.
Him: Oh. I thought it was a small. Crazy Americans.
(fyi. kid was born and raised in new york)

And then, like a mirage in a desert of shitty dates, crossing the street are my friends. I jump up! Oh look! It's my friends! Um...my friend is in town...and, I haven't seen her in years...and they're going to get drinks....
Him: So, you're gonna get rid of me, huh?
Me: Haha yeah.
Him: Will we ever see each other again.
Me: ohhh....you never know. I'll walk you back to the subway.

By the time we got to the subway I had quit trying.
Him: Well, I had a great time. I just couldn't believe this beautiful girl was giving me so many chances.
Me: Oh. yeah. Well, I'm glad you had a nice time.
(pause)
Him: Well, I hope you had a good time too.
Me: oooh...fnignaognrnew (that's me mumbling something about thanks for dinner).

And, as if all that wasn't enough, he would ask me these challenging questions. I think it was his poorly socialized way of trying to get more information, but it came across as almost antagonistic. He challenged me on why I have been unemployed for so long. I will take a lot of shit from a lot of dudes. To a point that it's almost a self-respect problem. But that shit? No. There are few things I hold sacred, unemployment is one of them. You just don't question it, you admire it.

And have I heard from him since? Of course. And I suspect it won't be the last time. I anticipate a check-in email within the week.